Thanks everyone - and Robert, welcome to the forum!
The pages that my son was working on were product-based, so the information was copy & paste for the most part. He has also worked on other pages, such as articles or archives that were also copy&paste with a bit of general formatting. Next, I will be teaching him the power of content syndication - both in finding (good) content and adding it to current sites... and in syndicating content we already have.
Basically, if I show him the steps, he can take over and repeat them until the project is done. He's been a big help so far in moving content over to my new template for SSWT!
As for having a hard time coming up with content... honestly, there is so much out there that is free to use - it seem like an endless supply! Also, I do enjoy writing (obviously lol), so I have tons of things already that I can turn into content. I also have a list here on my desk of topics I'd like to touch on - every time I think of one, I just jot it down on something... so there's never a shortage of anything to write about!